


Dating Advice

by levi_cas_tho



Category: Supernatural
Genre: Alternate Universe - High School, Fluff and Angst, Friends to Lovers, Happy Ending, Jealous Dean, Jealousy, M/M, Misunderstandings, Temporarily Unrequited Love
Language: English
Status: Completed
Published: 2017-08-27
Updated: 2017-08-27
Packaged: 2018-12-20 08:18:10
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,901
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11916879
Author URL: https://archiveofourown.org/users/levi_cas_tho/pseuds/levi_cas_tho
Summary: Just when Dean has figured out his not-so-platonic feelings for his best friend, Castiel drops the bomb that he has a crush on some guy. Really, it's just Dean's luck.Not only that, but now Cas needs advice on how to win the guy over.Just a quick one shot I came up with. I'm sure you guys can guess from the tags how this is gonna go ;)





	Dating Advice

“Sam, please, you know that wouldn’t end well.”

Dean frowned at Castiel’s distressed voice as he stepped into the kitchen, his groggy mind trying to catch up with what was going on. Cas had ended up spending the night last night so they could finish up their English project. Shurley’s class could be a real bitch sometimes, but they managed to scrape together a semi-decent presentation on Beowulf. I mean, how could they not, with Cas being such a fucking nerd?

“Why not? Trust me, Cas, I really think you have a shot at this—”

“A shot at what?”

Both Sammy and Cas whipped around to face Dean. Castiel immediately flushed, eyes wide and panicky.

“N-nothing, Dean. Sam and I were just discussing my breakfast making abilit—”

“Cas has a crush on someone!” Sam blurted out.

Castiel blanched and turned to glare at the younger Winchester. “ _Sam_ ,” he hissed.

Sammy shrugged innocently in response and activated his strongest form of puppy dog eyes. “What? He could help.”

Dean couldn’t move. Couldn’t even think. Goddammit, he had literally _just_ managed to get through his gay crisis and accept his feelings for his best friend, and Cas had to choose _now_ to take interest in someone else? Dean couldn’t even hide his pain behind denial anymore—he had already gotten through that stage. “Oh,” he said stupidly, suddenly realizing that he probably should have responded about 30 seconds ago. “That’s uh—wow.” Dean cleared his throat, trying to refocus. “What’s the deal then? You gonna ask him out or…?”

Castiel averted his gaze, suddenly seeming small and vulnerable as he stood there in his bumblebee pajama pants and black shirt. Dean gave him a lot of crap for his choice in clothing, but honestly, it was on Dean’s long list of what he loved about the guy. “Um, no. In fact, I see no reason for Sam to have even brought it up,” he said pointedly, throwing another glare at the thirteen-year-old.

Sam rolled his eyes, sitting up straighter from where he was perched on the countertop, legs swinging back and forth. “Cas, I’ve been trying to convince you to make a move for over a _year—_ ”

“ _What_? A _year_?” Dean choked out. He turned to glare accusingly at Castiel, who was looking more and more uncomfortable by the minute. “Cas, why didn’t you tell me about this? I’m your best friend, you know you can tell me anything, right? I’ve told you before that I don’t mind that you’re gay; you can talk to me about this kind of stuff.” The fact that Cas had chosen to tell _Sam_ before him was what really got to him. Yeah, Sammy and Cas had gotten pretty close over the years, but Dean had thought he and Cas were closer. They always joked about having a ‘profound bond’ and shit.

As though reading his thoughts, Cas took a step forward and shot Dean a reassuring smile. “I know, I know. I trust you, Dean, but its not that—I just, it’s embarrassing okay? And it’s not like anything is going to come from my foolish crush anyways, so I prefer not to dwell on it. I never intended on telling anyone about it either—Sam just figured it out on his own.”

This only made Dean feel worse. How could Sam notice and he not? Had he not been paying enough attention to Cas? Sam didn’t even go to their school—he was in middle school! How could he have possibly seen Cas interact with this mystery guy enough times to have put the pieces together. It didn’t make any sense. Dean shook his head, he could dwell on this stuff later. Right now he had to find a way to handle this situation.

“Look, uh Cas, if it’s been that long, it’s probably more than just a crush.” God, did that hurt to say. Maybe he could find a way to handle Cas having a simple fling, but if Cas was _in love_ with someone else? _Way to go, Winchester. You really missed your shot on this one._ Not that he even had a shot with Cas in the first place.

Castiel sighed heavily and rubbed his temple. “I know,” he begrudgingly admitted. “But trust me, nothing’s going to come of it anyways. There’s no way he could ever look at me that way, not when he’s so perfect and I’m so… so—”

“ _Cas,_ ” Dean said insistently, “ _you_ are the perfect one. I mean, you’re hilarious, and caring, and smart. For god’s sake, you’re the valedictorian, and you’ll probably still be when we graduate next year. _And_ you’re artistic—even though you don’t believe me, your art is fucking unbelievable man. Not to mention the fact that you’re gorgeous. I mean, between your big blue eyes and your lips and your sex-hair—”

Dean broke off when he realized what he was saying. Sammy looked like he was about a second away from laughing, and Cas was just staring at Dean with an unreadable expression, his face scarlet. Dean felt his own face heating up and cursed his lack of a filter. Dammit, he had just wanted to make Cas feel better, and instead he had to go and make a fool of himself.

“Look,” he said grumpily, shoving his hands into the pockets of his pajama pants, “what I’m trying to say is any guy would be lucky to have you. And if they don’t see it that way, well, they’re an idiot. Or blind. And they definitely don’t deserve you.”

When Dean scrounged up the courage to look up from the floor he saw Cas looking at him reverently, a glint of hope forming in his eyes for the first time during this godforsaken conversation. Dean belatedly realized he had probably just managed to convince Cas to run straight into the arms of that mystery guy. _Great._ Oh well. As long as Cas was happy, Dean could learn to suck it up. Hopefully.

“Anyways,” Sam said loudly, breaking the intense staring contest Dean and Cas had gotten into, “we need a plan to win this guy over. So, Dean, if someone were to try and woo you, would what they have to do?”

Dean bristled and shrugged dismissively before making his way to the counter. There was no way he could have this conversation without coffee. “I don’t know, man. I don’t see why it matters what _I_ would like. I mean, it would probably make more sense for me just to tell you what most dudes in general appreciate. Or for you to just tell me who this mystery dude is, that way I can tell you what I think he might dig.” Fuck. His hands were being all stupid and shaky. He quickly poured some coffee into his mug and wrapped his hands around his warmth in an effort to disguise the fact.

“Just humor me,” Sam said, looking at him curiously.

Dean rolled his eyes and gulped down a healthy amount of the too-hot liquid before responding. It burned as it made its way down his throat and he reveled in the sensation, wishing it was whiskey instead. “Fine, whatever,” he huffed. “If someone wanted to win me over, they should probably… uh… I don’t know—maybe something to do with Baby? Or classic rock? Those are two of my favorite things. Oh, you know what would be great? Pie! That’s a safe bet. Hell, that’s probably all they’d need. Well, actually, for them to even have a shot with me they would have to be able to get along with you, which is a challenge of its own.”

“Hey!” Sam protested. “Don’t be such a jerk.”

Dean chuckled and glanced at Cas, who was listening very intently to what Dean was saying. Dean honestly still didn’t understand the point of all this, but whatever. “They’d have to get along with you too, Cas. And if they’re really serious they should probably win over mom while they’re at it. She’s pretty easy to impress though. But yeah, that’s about it. Other than getting along with you guys, pie is all I’d need.”

“Really?” Cas asked skeptically. “That’s it? All I—er, _they_ would need to do is make you pie?”

Dean shrugged, finishing off his own cup of coffee before pouring another one for Cas. Black, with two spoonsful of sugar and three of honey—just how he liked it. How that guy didn’t have a mouth full of cavities was beyond Dean. “Well, yeah. But like I said, I doubt that’ll work on your guy. Maybe try flowers or something? Or concert tickets if you know what he likes? Honestly, if he has half a brain it shouldn’t take much to convince him to date you.”

He quickly finished adding in the honey and handed the mug to Cas, who gave him a gummy smile. “Thank you, Dean. For everything. I still doubt I could ever do enough to deserve him, but maybe… maybe I’ll give it a shot,” he said hesitantly. But there was a bit of hope mixed in there, too.

Dean just flashed him a tight smile and turned away under the premise of whipping up some more breakfast, but really, he just didn’t want Cas to see his weak-ass heart breaking.

\------

Cas ended up heading back to his own place after they finished eating breakfast (pancakes), leaving Dean to head up to his room and stew in his misery alone.

Throughout the whole five years he had known Cas, the guy had never dated anyone. I mean, he kinda had this weird thing with a guy named Balthazar a while back (thing meaning Balthazar would flirt and Castiel would become hopelessly flustered) but that was about it. Dean always thought it was strange, but Cas just claimed he knew what he wanted, and that those other guys weren’t it. Looking back, maybe Cas had had this crush going on since way back then.

Dean felt like a horrible friend. For one, he never even noticed his own best friend was in love with someone. He was always too busy chasing his latest conquest or looking after Sammy. Hell, despite the fact that he had still been in denial back then, the thought of Cas dating was never something Dean cared to think about. It always felt wrong to him, somehow. And making himself an even worse friend: he could not, for the life of him, force himself to be happy that Cas had found someone. He should be supportive, and instead he just felt sad and angry.

Damn if he’ll act that way around Cas though. No, he was gonna pretend to be the happiest, most supportive best friend in the world. If he managed to pull this off, he should get an Oscar.

Half of him hoped this didn’t work out, that Cas and the guy would break it off pretty soon after. But more of him knew that whatever Cas felt for this guy was pretty fucking strong. Really, he just wanted Cas to be happy. Even if it killed him.

\------

Dean awoke not even aware of when he had fallen asleep in the first place. His mouth was dry and his head had that weird fuzzy sensation going on that comes from waking up from a surprise nap in the middle of the day while not knowing what the fuck is going on. You know the kind.

He groaned and rubbed blearily at his eyes, not quite willing to wake up completely, when suddenly he heard the sound that must have woken him up in the first place. Someone was knocking on his door. Ugh.

“Come in,” he called out, voice still croaky.

“I, uh, can’t—my hands are otherwise occupied,” came the distant reply. Ah, Cas. What the fuck was he doing back here? Dean begrudgingly rolled out of bed and stumbled to the door, tripping over a blanket in the process. _Smooth, Winchester_.

He made it there eventually and fumbled with the handle before tugging it open with more force than strictly necessary. “Cas, what are you doing here, man? You literally just left.”

Cas squinted at him amusedly. He, unlike Dean, had changed out of his pajamas, and was now wearing jeans and a white t-shirt that said ‘Save the Bees’. “I’ve been gone for over five hours, Dean. It’s nearly three o’clock.”

“What? Since when—oh,” Dean cut off suddenly when he caught sight of what Castiel was holding. He had a bouquet of daisies in one hand and what seemed to be a fresh baked cherry pie in the other.

Cas was probably on his way to ask that guy out. Goddammit, Dean had hoped he would at least have until tomorrow to prepare—he had assumed Cas would make his move at school. Dean caught a whiff of the amazing scent from the pie, hunger mixing in uneasily with his jealousy. _Whoever Cas is after is one hell of a lucky guy._

Dean glanced up at Castiel’s face to see him with a sheepish, almost nervous expression on his face. “Dean?” he asked, voice small and unsure. “What do you think?”

“It’s great, Cas. Your guy is gonna love it. I’m not exactly sure why you went with pie since that would probably only work on me, but—”

“Dean _._ ” Dean looked up again to see Cas biting his lip. Fuck. “I’m not—this isn’t—” Castiel huffed in apparent frustration. If his hands were empty, he would probably be running one through his hair right now.  “These are for you,” he managed eventually, shoving the objects in Dean’s direction.

Dean’s heart skipped a beat for a moment before he realized what Cas probably meant. He crushed down the hope that had momentarily sprung up in his chest. “Oh, I see, this is like a trial run so you can practice for the real thing. That’s smart, Cas—”

“ _Dean,”_ Cas said insistently. An amused smile tugged at his lips. “These are for _you._ _You’re_ the guy I’ve had a crush on.”

Dean blinked. And blinked again. And rubbed at his eyes when the vision didn’t disappear. This had to be a dream, right? There’s no way Castiel Novak could possibly even look twice at him. This couldn’t be real.

Castiel’s hopeful smile slowly began to melt off his face, and he started gnawing on his bottom lip again. “Dean?” he prodded nervously. Dean couldn’t get his stupid mouth to work. Or his stupid brain, apparently. Castiel sighed, his gaze nervously flitting from Dean to the floor to the hallway. “You don’t feel the same way,” he said with a sad smile. “I really should have known better—I’m so sorry for all of this, but the way you were talking this morning… nevermind. I’m sorry.”

Cas haphazardly shoved the pie and flowers into Dean’s hands before starting to turn down the hallway. “Oh, wait.” He dug around in his pocket for a moment before pulling out two concert tickets. “Here. These are for you, too. They’re for a Black Keys concert a month from now—you can keep them. Maybe—maybe take a girl from school or something. I hope this doesn’t have to change anything between us—”

Dean’s brain was only just beginning to catch up with the situation, and panic bells were going off left and right. “Wait, what if I want it to change something?” he blurted out.

Cas’s face seemed to fall for a split second before he recomposed himself. “If that’s what you wan—”

“No, Cas, dammit—” Dean groaned in frustration and leaned back into his room to place the pie and flowers on the desk next to his door. Once that was done he returned his full attention to Cas, who looked full of regret. “Cas, listen to me,” he said gently, taking a cautious step forward. He could not mess this up. He would not mess this up. “I’m an idiot, this just caught me by surprise is all. Of course I wanna date you.”

Castiel squinted at him, hesitant to get his hopes up again. “But why? Why would you want—”

“Because everything I said this morning was true. And because I’ve liked you for a while now. I only just figured it out a couple weeks ago—that’s why I was so distant last month, I had a big gay freak out and everything. And I was hoping to work up the nerves to ask you out soon, but then you said you were interested in some guy and I thought I lost my chance.”

“Why didn’t you say anything? This morning?” Cas asked in disbelief.

Dean scoffed. “Are you kidding me? I wasn’t about to mess up my best friend’s chance to get with their crush by giving some ill-timed love confession. I just wanted you to be happy, no matter who you’re with.”

Castiel’s face broke out into a blinding smile. “You’re an idiot,” he said fondly, before surging forward to smash their lips together.

Dean let out a surprised ‘umpf’ that quickly turned into a moan as the kiss deepened. Unfortunately they had to pull back for air eventually, and Dean took the opportunity to drink in the sight of Castiel’s spit-slicked lips and messier-than-usual hair. “That is true,” he conceded, “but I’m _your_ idiot.”

\---

**_FIN_ **

**Author's Note:**

> That's all, my dudes. Hope you guy enjoyed! I know this title was mediocre, but if you guys have any ideas for a better one just let me know!


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